4-(4-Fluorobenzoyl)piperidine → HCID 178453902, compound

HRID 1664952Notes

Reaction equation

HRID 1664952 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[C:16]([O:20][C:21](=[O:32])[NH:22][C@H:23]1[CH2:28][CH2:27][C@H:26]([CH2:29][CH:30]=O)[CH2:25][CH2:24]1)([CH3:19])([CH3:18])[CH3:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:16]([O:20][C:21](=[O:32])[NH:22][C@H:23]1[CH2:24][CH2:25][C@H:26]([CH2:29][CH2:30][N:11]2[CH2:12][CH2:13][CH:8]([C:6](=[O:7])[C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:15][CH:14]=3)[CH2:9][CH2:10]2)[CH2:27][CH2:28]1)([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 27244404-(4-Fluorobenzoyl)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 178453924HCID 178453924, compound

Product 1

HCID 178453902HCID 178453902, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 4-(4-fluorobenzoyl)piperidine (0.850 g, 3.4 mmol), Trans-[4-(2-Oxo-ethyl)-cyclohexyl]-carbamic acid tert-butyl ester (0.926 g, 4 mmol), in 1, 2 dichloroethane (10 mL) was stirred for 4 h at room temperature and sodium triacetoxyborohydride (1.33 g, 6 mmol) was added and the resulting solution was stirred for 12 hours until the TLC indicated completion of the reaction. The mixture was filtrated and concentrated to dryness and purified with column chromatography on silica gel using CH2Cl2—CH2Cl2/MeOH (1-9:1). The product fractions were concentrated to give 1.4 g (3.25 mmol, 93.2% yield) of a light yellow solid. MS (m/e): 433.4 (M+H+).

Workup

  1. customcompletion of the reaction
  2. filtrationThe mixture was filtrated
  3. concentrationconcentrated to dryness
  4. custompurified with column chromatography on silica gel
  5. concentrationThe product fractions were concentrated

Sources & evidence

ORD record
ord-6946743d2d1e4385bc5aa08dcf320e27
Source dataset
uspto-grants-2011_10
Patent number
US08039490B2

Reaction notes

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